PHOTOINDUCED MOLECULAR-TRANSFORMATIONS .123. ONE-STEP SYNTHESIS OF 1H-BENZ[F]INDOLE-4,9-DIONES BY A NEW REGIOSELECTIVE PHOTOADDITION OF 2-AMINO-1,4-NAPHTHOQUINONE WITH VARIOUS ALKENES AND ITS APPLICATION TO ONE-STEP SYNTHESIS OF KINAMYCIN SKELETON

被引：25

作者：

KOBAYASHI, K ^{[1
]}

TAKEUCHI, H ^{[1
]}

SEKO, S ^{[1
]}

SUGINOME, H ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC ENGN,DIV ORGAN SYNTH,SAPPORO,HOKKAIDO 060,JAPAN

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 05期

关键词：

D O I：

10.1002/hlca.19910740518

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2,3-Dihydro-H-1-benz[f]indole-4,9-diones are formed in one-step in 45-82% yields by an unprecedented [2+3]-type regioselective photoaddition of 2-amino-1,4-naphthoquinone with various electron-rich alkenes and the [2+3] adducts derived from aminonaphthoquinone with vinyl ethers and vinyl acetate to give H-1-benz[f]indole-4,9-diones including a benzindole-dione with a kinamycin skeleton in 33-72 % yields. A probable pathway leading to the formation of the dihydroindole-dione involving air oxidation of an intermediary hydroquinone is proposed.

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页码：1091 / 1094

页数：4

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